


Jesse Ventura

by orphan_account



Category: RedLetterMedia RPF
Genre: Anal Fingering, Anal Sex, Buckle up, Dirty Talk, F/M, Fluff and Smut, MILD - Freeform, Oral Sex, Overstimulation, Pegging, Reader doesn't have a dick, Smut, but is not necessarily female, that's right boys
Language: English
Status: Completed
Published: 2020-03-24
Updated: 2020-03-24
Packaged: 2021-02-28 18:28:32
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 3,990
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/23291719
Author URL: https://archiveofourown.org/users/orphan_account/pseuds/orphan_account
Summary: You knew he wanted it;heknew he wanted it.Now, if Jay would just calm down and let ithappen.
Relationships: Jay Bauman/Reader, Jay/Reader
Comments: 14
Kudos: 31
Collections: Red Letter Media Fanfic Quarantine Collection





	Jesse Ventura

**Author's Note:**

> i could work on the story i already have started. i could go to sleep, since it's past midnight and i have work at five-thirty in the morning. i could work on my several-classes-worth-of homework.
> 
> but instead i methodically wrote about giving jay bauman the strap.
> 
> this is. astoundingly sloppy.
> 
> sorry! ¯\\_(ツ)_/¯

Your arms were crossed, and Jay sat across from you, mirroring your position. The only difference between your respective poses were your expressions: you had a self-satisfied almost-smirk, and he had that cute little grumpy “ >:T ” facial expression of his that you loved.

“So,” you began for him, leaning forward and bouncing your feet in front of your chair.

He huffed out a sigh and slid back into his seat, spreading his legs and making his jeans stretch tight over them.

The two of you sat in silence for a moment. His leg bounced. Your eyes cast over his face; his eyes avoided yours. Then you dropped your arms from across your chest and the smug expression from your face. “Jay,” you started, softer, “we don’t have to do this if you don’t want to.”

As eager as you were to do this for him, you knew that he was not someone who took too kindly to being forced into something he didn’t want. You knew he wanted it; _he_ knew he wanted it. Still, he had such a tight rein on his control that you knew this whole situation was causing a bit of a war in his head. Subtle though his dominant tendencies were, it was still a lot to ask of him to cede so much power in such an intimate way.

The two of you had only started legitimately talking about it recently—before that, the only mention of it had been one night when he had gotten _catastrophically_ wasted while shooting an episode of BotW. You’d had to go pick him up from the lot, and his face was red from giggling and he’d had tear tracks down his cheeks and you just wanted to keep him that happy and carefree always. After you helped him into your car and then climbed in the passenger seat, Mike had screeched at you nonsensically about not letting him strangle any cats. Pulling from the lot and heading to Jay’s, he’d burst into a fresh batch of giggles. He was dazzling.

You’d gotten him home safe and sound, helped him out of his jeans, and put him in bed. You left to grab him a water bottle, and upon returning, he’d taken the bottle from your hands, set it aside, and pulled you into the bed on top of him, trying to lock his way into your mouth. Laughing softly, you’d informed him that he was _far_ too drunk to fuck you.

Jay had just hummed, rubbing his thumbs over your hipbones. “I don’t want to fuck you,” he’d started, rolling his hips in a contradictory manner. He’d then grabbed you by the back of your hair, pulled you down so your ear was next to his mouth, and followed it with a whispered, _“I want you to fuck me.”_

A shudder had wracked your spine, from the thrill of the idea and the feeling of his stubble on your earlobe, which he’d then tried to capture with his teeth. _Jay wanted you to give him the strap_. You’d climbed off of him, calmed yourself, and finally convinced him to sleep, but the idea had never left your mind.

You waited for him to mention it, but he didn’t. Not the next day, week, or month. You knew that he hadn’t blacked out that night, so you assumed that he was embarrassed by his request. Did he think you weren’t interested? _God,_ that sure wasn’t a fucking problem. The idea of fucking Jay had completely consumed your thoughts.

In the end, you brought it up yourself a little over two weeks ago. A little unfairly, you breached the subject _while_ you two were having sex. 

You had been riding him, Jay sitting cross-legged and you straddling him while his stubble burned the skin covering your collarbones. Often, your mouth ran away from you when you got _really_ horny, and in this instance, you’d grabbed Jay’s chin, licked between his open lips, and said right into his mouth, “You fill me up _so_ fucking good, Jay. _Mmm,_ goddamn, imagine how fucking good you would feel if you let _me_ stretch you open like this, baby.” You’d heard a hard gasp, and then Jay was _coming_ , shaking with his fingernails almost breaking the skin of your hips.

Yeah, that just about opened the floodgates of pegging conversation. Then, finally, after a shockingly awkward start, you two were prepared to do it. He, being the control-freak he is, started researching on the best ways for him to prepare himself, and together you’d picked out a strap that you both liked. You’d planned this day, cleared your schedules, and were ready to get down to fuckin’ business.

That is, of course, if Jay would just calm down and let it _happen._

He sighed again, uncrossing his arms to scrub his hand across his beard. “We both know I want to do it,” he said, echoing your thoughts. “My brain just isn’t eager for me to put that kind of power in someone else’s hands.”

Now it was _your_ turn to sigh. “Kid, you know that being the one penetrating or penetrated has nothing to do with power—”

Jay rolled his eyes and waved his hand at you, “Yeah, yeah, I know. Don’t call me kid.”

You smiled, then got up from your chair and crossed to stand in front of him. He leaned forward to rest his head on your stomach. Bringing your hands up to his hair, you scratched your fingers through it til all the gel was gone, ignoring his grumble of protest. Using a gentle grip on his hair, you tugged his head back until you could kiss his forehead. 

You mumbled against his skin, “Let me take care of you, yeah?”

Jay let out a big breath through his nose, then nodded, and pulled you into his lap to kiss you. You smiled into the kiss, settling your knees on either side of his hips and letting your weight rest in his lap. This kiss was slow; you were trying to calm him down before you riled him up, and his hands slid from the backs of your thighs to the small of your back. His beard was soft against your chin, and you slid your tongue between his lips and felt his shoulders slide out of their tense position near his ears.

Your hands glided down his neck, to his shoulders, and back up to his scalp again, scratching your nails across its surface. Jay shivered below you, and a smile tugged at the corners of your mouth before you really started kissing him, using your grip on his softened hair to tilt his head for better access. Jay relocated one of his hands to your ass, bringing you down to grind on him where he was _already_ half-hard, just from the anticipation. Humming happily into your kiss, you stripped his denim jacket off of your shoulders and quickly reached for his t-shirt, sliding it up so you could run your fingers through the hair on his chest.

Jay removed his hands from you only long enough to rid you both of your shirts, then he relocated his hands to your ribs, feeling the way they undulated while you ground your hips into his. One of his hands slid towards your ass again, then stopped when he came into contact with the harness where it was peeking out from the tops of your jeans. His mouth had paused against yours, and you licked across his lips before sinking your teeth into his bottom lip. He shuddered again, pulling out the elastic of the harness strap before snapping it against your skin.

You yelped, and he laughed. Swatting his shoulder, you got out of his lap, pulling him to stand before shoving him down again, onto the bed this time. Jay pushed himself onto his elbows, looking at you with those cute little bunny teeth in his lip. You put your knee on the bed for just a minute so you could kiss him again before you leaned back to undo his jeans and begin pulling them down those delicious thighs of his. He reached for the button on your jeans, but you slapped his hand away.

“Jeez, you buy one strap-on and all of a sudden you’re a goddamn sexual Tyrannosaurus,” he chuckled.

You sucked a mark into his thigh until he let out that little gasp you love, then responded, “You’re looking a little slack-jawed there.” Jay laughed, slightly breathless, though you could tell that some of the tension had returned to his shoulders.

A pleased hum replaced his laugh when you rid him of his boxer-briefs and nuzzled against his now-mostly-hard dick. You slid to your knees at the end of the bed and held him up straight, flicking your tongue against the little circumcision scar before taking the head in your mouth. This time, you let out the pleased hum as you sucked the first bead of precome off of him.

Jay slid down onto his back, and you smiled around his cock. You wanted to keep him as relaxed as you could, and if that required some blow-job bribery, you would happily take advantage of it. His hand wound its way into your hair, not pulling, just playing with the strands while you bobbed your head and rubbed your thumb under the base of him. Your other hand rubbed little circles into his right thigh. Every time he let out a sigh and melted further into the mattress, you considered it a little victory. 

You pulled off of his cock for a minute, moving your hand around the base of him to the tip, causing him to let out a wavery little moan. Jay’s hand fell to the bed, his knuckles clenching. Looking by the chair you were sitting in earlier, you reached into the backpack you had set beside it, just grabbing the tube of lube for now. You returned to Jay, finding his eyes closed and his hips making little twitches up into your fist. You switched to your non-dominant hand, slowed your stroking, and mouthed at his balls while opening the lube with your free hand.

Jay didn’t seem to notice the sound of the lube opening, but he sure noticed the two freshly-lubed fingers sliding up his thigh towards his hole. Instantly trying to combat his tension, you took his cock back into your mouth as you started stroking your index finger across his hole. His hands were white-knuckling the sheets. With a little hum, you backed off your mouth to just the tip of him, swirling your tongue until he relaxed enough for you to start sliding your finger in.

Jay’s eyes were squeezed shut. You stopped yourself with half a finger in; not pulling it out, just letting it rest. You pulled off his dick, twirling your thumb around the head while you peppered kisses along his lower stomach. “Jay.”

He opened his eyes, and they glanced at you for a second before looking up at the ceiling. His jaw was clenched. “ _Jay._ ” His eyes returned to yours and stayed. “Let me in, pretty boy.” Holding your eyes for one more second, he took a deep breath, unclenched his jaw, and let his head fall back into the mattress. As he exhaled, he relaxed around your finger, and you resumed your slow slide into him, returning to his softening dick with twice the fervor.

You just left your finger there for a moment, waiting for him to give the go-ahead. You knew he’d been practicing on himself, but he didn’t do it while you were around. Fortunately, your fingers were significantly smaller than his, so it’d probably be easier for him to adjust to the foreign intrusion. After a minute of nothing but the sounds of you sucking him, he sighed again, and quietly said, “You can move.”

Swallowing around the head of him, just to get him to hum, you twisted your finger, then began slowly drawing it out and sliding it back in. Jay’s eyes were open, and his brow was furrowed for the first dozen or so slow strokes, but once you started reaching for his prostate, his brow eased out, and his lips parted when you grazed it. His cock jerked in your mouth, and you laughed around him. Your index finger was too short to fully reach it, so after a couple more minutes of letting him adjust, you removed your mouth from him to ask if you could put in another. 

Barely hesitating, Jay nodded, and you pressed your smile into his stomach. You pulled out your finger slowly, suppressing a shiver when you felt him cling to you. You rubbed your fingers together for a minute to warm up your middle finger then brought them both to his entrance. He eased up after just a moment this time, and you eased your fingers inside of him, hearing him let out a breath that became a hum.

Instead of returning to his cock, you pulled one of his balls into your mouth, sucking gently as your fingers bottomed out inside of him. He didn’t wait nearly as long to nod his permission for you to move, and you twisted your fingers again before starting to thrust. It was far easier to glide across his prostate with your middle finger, and Jay started letting out these little half-moans, like he was trying to silence himself. You allowed it for the moment, then increased your tempo. Jay flat-out moaned this time.

“Oh, _fuck,_ ” he whispered, returning his hand to our hair when you put your mouth back on his cock. His hand was trembling, and his cock was pulsing on your tongue. You felt heady with the knowledge that _you_ were doing this to him; _you_ had Jay shaking like a leaf. You were suddenly overcome with the urge to have him begging before the night was over.

“Are you ready for a third one?” Your voice had gotten thick with saliva from sucking his cock.

Jay mumbled out a deep _“yeah”_ and you eased your fingers out again so you could add more lube. His fingers clenched in your hair, and you shook out the cramp in your hand before putting on the new layer of lube and quickly bringing your fingers back to where he had started getting loose for you. You didn’t wait for him this time; you pushed your fingers into him, a little faster, and he hissed at the stretch before moaning for it. You separated your hand from his cock. Jay didn’t seem to notice.

With your free hand, you reached towards your bag again, pulling out another, smaller drawstring bag. Jay muttered an encouragement for you to start fingerfucking him with your three fingers, and you sunk your teeth into his thigh while you opened the bag to remove the actual dildo for your strap-on. It was a bright slime green like the “HORROR” pin he had on his jacket, and you stuffed it between your thighs to get it warmer. 

Looking back up at Jay, you saw his face fully relaxed, his hands no longer gripping the sheets or your hair, just laying limp by his body. His cock was lying hard against his stomach, leaking out precome. He had started lifting his hips to meet your fingers, and you bit back a moan, just watching him for a moment before you curled your fingers towards his prostate and he _whined_.

 _Jesus fucking Christ,_ you thought, _we have to do this, like, weekly._

You slowed your thrusts, ignoring Jay’s little grumble, grabbed the dildo from between your thighs, and stood up, reluctantly pulling your fingers from him. Leaning across him, you kissed him hard, and it took him a minute to respond, but then he brought his hands to your hips and squeezed hard. You placed the dildo on the bed. It rolled into Jay’s thigh, and he shivered, before reaching unsteady hands to unfasten your jeans. You weren’t kissing him so much as licking into his slack mouth. Again, you were overcome with the knowledge that you were pulling him apart like Captain Rhodes, and he was just _letting you_. Not only that, but he was _loving_ it.

For the first time, you noticed just how fucking turned on you were. Jay’s hand was inside your jeans, rubbing at you with no coordination, and you probably could’ve come from it, but tonight wasn’t about you. Grabbing his hand, you separated from his lips and pulled his fingers to your mouth, licking the wetness from them. Jay’s half-lidded eyes followed the movement, and you leaned back to his mouth to trade the taste with him, both of you moaning into each others’ mouths.

Pulling back from his lips, you ask him to roll over onto his hands and knees. He nods, and immediately sets to it. You’d’ve loved to do this face-to-face, but you didn’t have much experience with this, and you figured this would be the easiest way to start off. You stood back to shuck off your jeans, then you grabbed the dildo and settled it into the space on your harness. Once it was set, you looked back at Jay, feeling your knees get weak.

He looked _so good,_ and you were officially worried that you’d become addicted to having him like this. He had that totally-unfair-straight-guy-bubble-butt, and you could see his hole wet and loose between his cheeks. You could’ve sworn you felt a phantom pulse in your phantom erection, like a lost limb. Seeming to grow self-conscious of the lack of contact, Jay turned his head shyly over his shoulder to look at you. You guess he saw something he liked, cause he shuddered and turned face-forward again.

Finally, you climbed on the bed behind him. You popped open the cap on the lube you’d grabbed from the floor and emptied what was likely far too much into your hand. Setting the lube aside, but within reach, you started coating your pseudo-cock in slick, grabbing one of Jay’s cheeks with your free hand.

Apparently, the loss-of-mouth-control decided to strike just then, and you said without thinking, “I wanna lick you open.”

Jay’s head dropped forward. “Fuckin’ _shit_. Next time.” Your mind shorted out at the idea of getting to do this to him again. “I think I’d actually die if you did that right now.”

You spread him open with the hand on his cheek and knee-walked into place. “Die doing what you love?” You positioned the head of the dildo at his hole.

He let out a shaky laugh. “Just might die anyway. My safeword is Breen.”

“Mine is ‘keep going.’” Jay started laughing, and without warning, you started gliding into him. He choked on his laugh, and his stomach dropped into an arch you didn’t think a straight guy was capable of.  
Both of your breath shuddered out of the two of you the instant you bottomed out, and you stilled your hips, rubbing your hands over Jay’s back and shoulders, pressing kisses into his spine. “Do you need a minute?”

Jay’s voice was tight when he responded with a “yeah.” You draped yourself over his back, feeling where he’d perspired, feeling the hair on his legs touching yours, feeling the way he trembled. You couldn’t imagine everything _he_ must be feeling.

“Okay,” he began, voice a little stronger. “I’m ready.”

A deviant smile spread across your lips. “Ready for what?” you asked into his shoulder.

“Oh, you fucking asshole,” he started, and you gleefully interrupted with, “I sure am!”

Jay’s shoulders started shaking with laughter, and you joined in, letting the atmosphere lighten to something more playful. You scratched your nails across his scalp again, waiting for his laughter to subside. When it did, you told him, “I’m going to start fucking you now, okay?”

Letting out a little hum and shaking his head, Jay reassured: “Yeah, fuck me.”

 _My pleasure,_ you thought. Moving your hands to his hips, you leaned back. Then, you slowly drew your hips back, and snapped them forward with little finesse.

Jay moaned anyway. You moaned with him, pulling back for another thrust. You almost pulled all the way out, but managed to stay in before re-entering him with far more success, which Jay made very audible. After that, it became much easier.

Since your hips weren’t used to this type of movement, you mostly leaned back and used your hands to pull yourself into and out of Jay. You wouldn’t be able to tell you were struggling, though, what with the noises he was making. “God damn,” he ground out, and you fought back a shudder, worried that one wrong movement would dislodge you now that you’d found a groove.

“God _damn,_ ” he reiterated, head hanging between his shoulders, hips unconsciously twitching back onto that fake cock. You moaned at the display, letting him fuck himself onto you. _No wonder high school boys only want one thing,_ you thought, _I would never stop thinking about this if I were them._

No longer wanting to be passive, you spread your thighs and started fucking Jay harder. His moans became more frequent, interrupted with the sound of your pelvis slapping into his, and you were _drunk_ off of this. “I haven’t stopped thinking of this for _months,_ Jay,” you confessed to him. He tried to hold in his moans to listen to you better.

“I’ve been thinking about fucking this perfect ass of your since you first mentioned the idea. I can’t believe how lucky I am, getting my cock inside you like this,” you babbled, and Jay _couldn’t_ hold his moans in, you were fucking them out of him. You reached under him for his dick, feeling him drenched in his own precome.

Knowing you didn’t have the coordination to fuck him and jerk him off, you just tried to hold you fist still and fuck him forward into it. You saw him start to clench his ass; he was close, and you wanted him to come on your cock _so fucking bad_.

You leaned as far forward as you could while still retaining balance to keep your hips going, and almost moaned out, “I just wish I was able to fill you with my come like I’m filling you with my cock.”

Jay’s cock fucking _leaped_ in your hand, come shooting all over his bed, his moaning so loud that you thought he might scare the cat in the hallway. He panted and shook, and you could almost feel how hard he was clenching that fake cock inside of him. You twisted your hand a bit and felt him shudder with overstimulation, then you dropped your hand and stopped your hips, not pulling out yet. 

You pressed your chest to his back, listening to his breathing become more and more even. When his pulse had slowed to a more manageable level, you slowly withdrew the dildo from him. You kissed his back while you unbuckled the straps to your harness and dropped it off the bed, not concerned about the mess.

Pulling Jay up to your chest, you yanked down the comforter so he wouldn’t have to lay down in his drying come, then crawled up beside him so you could lay down together.

Jay didn’t speak for a while, and just when you thought he’d fallen asleep, he said “We can’t do that too often. I think I’ll go blind.”

You released a breath you didn’t know you’d been holding with your soft laugh. “Was it okay?”

“‘Okay?’” he asked, pulling you to lay your head on his chest. “It was so good that I don’t think I’ll be able to make eye contact with a religious official for the next three months.”

You buried your smile in his chest.

**Author's Note:**

> also this is the longest fucking fic i've written to this date. i have no idea what the fuck came over me.


End file.
